Bromine → 5-Bromo-2-hydroxy-3-methylpyridine

To a solution of 2-hydroxy-3-methylpyridine (0.500 g, 4.58 mmol, Acros Organics) in DCM (15 mL) was slowly added bromine (0.282 mL, 5.50 mmol). After addition, the mixture was stirred at rt for 18 h. The mixture was cooled to 0° C. and was quenched with saturated aqueous NaHCO3 (5 mL). The mixture was then extracted with EtOAc (3×20 mL). The combined organic layer were dried over MgSO4 and concentrated. The residue was then dissolved in MeOH (20 mL) and silica gel was added. The mixture was concentrated and dried in vacuo. The resulting mixture was then purified by silica gel flash column chromatography (solid loading, 0%-100% EtOAc/hexane) to afford the title compound as a light pink solid. MS (ESI, positive ion) m/z: 188, 190 (M+H).

1. additionAfter addition
2. temperatureThe mixture was cooled to 0° C.
3. customwas quenched with saturated aqueous NaHCO3 (5 mL)
4. extractionThe mixture was then extracted with EtOAc (3×20 mL)
5. dry with materialThe combined organic layer were dried over MgSO4
6. concentrationconcentrated
7. dissolutionThe residue was then dissolved in MeOH (20 mL)
8. additionsilica gel was added
9. concentrationThe mixture was concentrated
10. customdried in vacuo
11. customThe resulting mixture was then purified by silica gel flash column chromatography (solid loading, 0%-100% EtOAc/hexane)

ORD record

ord-ed0f05a22fa340c490d9fcf103988fa5

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710043B2